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Cheap flights from Illinois to Anguilla from $573

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Anguilla departing on 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

American Airlines Logo
7:04 am - 4:05 pmORD-AXA
7h 01m1 stop
American Airlines Logo
5:25 pm - 8:59 amAXA-ORD
17h 34m1 stop
$573American Airlines
Find Deal
Wed, Jan 28 - Fri, Feb 6
American Airlines Logo
5:10 am - 4:05 pmORD-AXA
8h 55m2 stops
American Airlines Logo
5:25 pm - 7:30 amAXA-ORD
16h 05m2 stops
$577American Airlines
Find Deal
Wed, Jan 28 - Fri, Feb 6
American Airlines Logo
7:07 pm - 2:18 pmORD-AXA
17h 11m1 stop
American Airlines Logo
5:19 pm - 12:21 amAXA-ORD
9h 02m1 stop
$598American Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
7:07 pm - 2:18 pmORD-AXA
17h 11m1 stop
American Airlines Logo
5:19 pm - 7:05 amAXA-ORD
15h 46m2 stops
$602American Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
7:07 pm - 4:39 pmORD-AXA
19h 32m1 stop
American Airlines Logo
5:05 pm - 9:25 amAXA-ORD
18h 20m1 stop
$612American Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
American Airlines Logo
5:00 am - 2:18 pmORD-AXA
7h 18m1 stop
American Airlines Logo
2:58 pm - 12:21 amAXA-ORD
11h 23m1 stop
$628American Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 22
American Airlines Logo
8:45 pm - 2:18 pmORD-AXA
15h 33m2 stops
American Airlines Logo
5:05 pm - 6:40 amAXA-ORD
15h 35m2 stops
$632American Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 22
Logo
8:52 am - 5:15 pmORD-AXA
31h 23m2 stops
Logo
9:35 am - 8:03 pmAXA-ORD
35h 28m2 stops
$1,864
Find Deal
Thu, Aug 28 - Tue, Sep 2
United Airlines Logo
6:21 pm - 5:35 pmORD-AXA
21h 14m2 stops
United Airlines Logo
9:46 am - 11:44 pmAXA-ORD
15h 58m2 stops
$4,713United Airlines
Find Deal
Wed, Dec 24 - Mon, Dec 29
United Airlines Logo
9:15 pm - 5:35 pmORD-AXA
18h 20m2 stops
United Airlines Logo
9:46 am - 11:44 pmAXA-ORD
15h 58m2 stops
$4,863United Airlines
Find Deal
Sun, Dec 21 - Sun, Jan 4

American Airlines flights from Illinois to Anguilla

Our best American Airlines deals on Illinois to Anguilla flight tickets
American Airlines
Jan 28
ORD7:04 amChicago O'Hare Intl
7h 01m
1 stop
AXA4:05 pmThe Valley Wallblake Intl
Feb 6
AXA5:25 pmThe Valley Wallblake Intl
17h 34m
1 stop
ORD8:59 amChicago O'Hare Intl
$573
Find similar
American Airlines
Jan 28
ORD5:10 amChicago O'Hare Intl
8h 55m
2 stops
AXA4:05 pmThe Valley Wallblake Intl
Feb 6
AXA5:25 pmThe Valley Wallblake Intl
16h 05m
2 stops
ORD7:30 amChicago O'Hare Intl
$577
Find similar
American Airlines
Nov 8
ORD7:07 pmChicago O'Hare Intl
17h 11m
1 stop
AXA2:18 pmThe Valley Wallblake Intl
Nov 15
AXA5:19 pmThe Valley Wallblake Intl
9h 02m
1 stop
ORD12:21 amChicago O'Hare Intl
$598
Find similar

United Airlines flights from Illinois to Anguilla

Our best United Airlines deals on Illinois to Anguilla flight tickets
United Airlines
Dec 24
ORD6:21 pmChicago O'Hare Intl
21h 14m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Dec 29
AXA9:46 amThe Valley Wallblake Intl
15h 58m
2 stops
ORD11:44 pmChicago O'Hare Intl
$4,713
Find similar
United Airlines
Dec 21
ORD9:15 pmChicago O'Hare Intl
18h 20m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Jan 4
AXA9:46 amThe Valley Wallblake Intl
15h 58m
2 stops
ORD11:44 pmChicago O'Hare Intl
$4,863
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 7, 2025.
Use the filters below to find and compare flights from Illinois to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 1/28

7:04 am-4:05 pm

1 stop7h 01m

The Valley Wallblake Intl

Fri 2/6

5:25 pm-8:59 am

1 stop17h 34m

$573

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 1/28

5:10 am-4:05 pm

2 stops8h 55m

The Valley Wallblake Intl

Fri 2/6

5:25 pm-7:30 am

2 stops16h 05m

$577

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 11/8

7:07 pm-2:18 pm

1 stop17h 11m

The Valley Wallblake Intl

Sat 11/15

5:19 pm-12:21 am

1 stop9h 02m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 11/8

7:07 pm-2:18 pm

1 stop17h 11m

The Valley Wallblake Intl

Sat 11/15

5:19 pm-7:05 am

2 stops15h 46m

$602

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 11/14

7:07 pm-4:39 pm

1 stop19h 32m

The Valley Wallblake Intl

Fri 11/21

5:05 pm-9:25 am

1 stop18h 20m

$612

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 11/11

5:00 am-2:18 pm

1 stop7h 18m

The Valley Wallblake Intl

Sat 11/22

2:58 pm-12:21 am

1 stop11h 23m

$628

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 11/11

8:45 pm-2:18 pm

2 stops15h 33m

The Valley Wallblake Intl

Sat 11/22

5:05 pm-6:40 am

2 stops15h 35m

$632

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 8/28

8:52 am-5:15 pm

2 stops31h 23m

The Valley Wallblake Intl

Tue 9/2

9:35 am-8:03 pm

2 stops35h 28m

$1,864

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 12/24

6:21 pm-5:35 pm

2 stops21h 14m

The Valley Wallblake Intl

Mon 12/29

9:46 am-11:44 pm

2 stops15h 58m

$4,713

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 12/21

9:15 pm-5:35 pm

2 stops18h 20m

The Valley Wallblake Intl

Sun 1/4

9:46 am-11:44 pm

2 stops15h 58m

$4,863

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Anguilla from

How to get the cheapest flight ticket from Illinois to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Anguilla?

The cheapest day to depart from Illinois to Anguilla is on a Friday when prices can be found for as low as $650. The most expensive day to fly to Anguilla is Saturday, with ticket prices averaging around $990.

What is the cheapest time of day to depart on your flight to Anguilla?

Flying to Anguilla from Illinois in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $607 when looking at flights departing in the afternoon. Flights in the morning are often more expensive with an average ticket price of $759.

Cheap Illinois to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Anguilla

Best Price Found

$573

Fastest flight time

7h 01m

Direct flights

None

Airports in Anguilla

1 airport
The best flight deal from Illinois to Anguilla found on momondo in the last 72 hours is $573
The fastest flight from Illinois to Anguilla takes 7h 01m
There are no direct flights from Illinois to Anguilla. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - The Valley Wallblake Intl Airport.
There is 1 airport near Anguilla: The Valley Wallblake Intl (AXA)
Search flight deals

  • When did momondo last update prices for flights from Illinois to Anguilla?

    Prices for flights from Illinois to Anguilla refresh daily.

  • How many operators does momondo search for flights from Illinois to Anguilla?

  • How old do you have to be to fly from Illinois to Anguilla?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Anguilla.

  • What documentation or ID do you need to fly to Anguilla?

    The required travel and health documents for your Anguilla trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Anguilla. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Anguilla

Compare and see reviews for airlines that fly from Illinois to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $629Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Anguilla?

It is quick and easy to find Illinois to Anguilla flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Anguilla that suits you.

Can I find flights from Illinois to Anguilla with flexible booking policies on momondo?

All flight searches from Illinois to Anguilla on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Illinois to Anguilla?

momondo provides multiple filters to help you find the best flight to Anguilla from Illinois. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Illinois to Anguilla right now. Can momondo alert me if prices change?

Price alerts on flights to Anguilla from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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